Sodium Methoxide → HCID 178450811、化合物

HRID 2169359ノート

反応式

HRID 2169359 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:13][C:14]([NH2:16])=[NH:15])[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl.C1(C2(CC(N)=N)CCCC2)C=CC=CC=1.[C:33]([O:37][C:38](=[O:53])/[C:39](/O)=[C:40](\[O:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)/[C:41](O)=[O:42])([CH3:36])([CH3:35])[CH3:34].C[O-].[Na+]>CO.C(OCC)(=O)C.CCCCCC>[C:33]([O:37][C:38]([C:39]1[C:40]([O:44][CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)=[C:41]([OH:42])[N:16]=[C:14]([CH2:13][C:8]2([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[CH2:12][CH2:11][CH2:10][CH2:9]2)[N:15]=1)=[O:53])([CH3:36])([CH3:34])[CH3:35]

参加物

8

反応物 4

HCID 10942334Sodium MethoxideHCID 867258072-(1-Phenyl-cyclopentyl)-acetamidine HCl saltHCID 867258102-[1-(4-Chlorophenyl)-cyclopentyl]-acetamidineHCID 86725882(E)-2-benzyloxy-3-hydroxy-but-2-enedioic acid 4-tert-butyl ester

生成物 1

HCID 178450811HCID 178450811、化合物収率 91%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
0 °C

実験手順

To a stirred solution of 2-[1-(4-chlorophenyl)-cyclopentyl]-acetamidine; hydrochloride (322) (3.1 g, 11.34 mmol) in methanol (25 mL) was added (E,Z)-2-benzyloxy-3-hydroxy-but-2-enedioic acid 4-tert-butyl ester 1-methyl ester (4) (4.19 g, 13.61 mmol) and cooled to 0° C. To this reaction mixture was then added sodium methoxide (25% in methanol) (7.4 mL, 34.03 mmol) and stirred at room temperature for 16 h (TLC; ethyl acetate:hexane=1:1, Rf=0.5). The reaction mixture was diluted with ethyl acetate (300 mL), washed with water (60 mL) and brine (60 mL) and dried and concentrated in vacuo to get crude mass which was purified by CombiFlash eluted with gradient polarity mobile phase (hexane to 50% ethyl acetate in hexane) to get pure 5-benzyloxy-2-[1-(4-chlorophenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid tert-butyl ester (323) (5.1 g, 91%) as a light brown solid.

後処理

  1. washwashed with water (60 mL) and brine (60 mL)
  2. customdried
  3. concentrationconcentrated in vacuo
  4. customto get crude mass which
  5. customwas purified by CombiFlash
  6. washeluted with gradient polarity mobile phase (hexane to 50% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-484d261894284809ab340e823713ac9f
出典データセット
uspto-grants-2015_06
特許番号
US09045486B2

反応ノート

読み込み中…